SYP Next Steps and Deadlines

In Youth by Ashton Wollett

COVID-19 Refund and Payment Policies
In view of the current uncertainties, Courageous has made amendments to the refund and payment policy for the summer of 2021. This year, we will be waiting to send out payment links until a later date when we have more information about whether the season will be delayed or amended in some way. We also understand that many are experiencing some economic hardship. To help with this, we will be offering flexible payment plans. Furthermore, should summer programs be unable to be safely run, Courageous will be offering full refunds to all families. We continue to remain hopeful and are moving forward AS IF we will be running fully in-person with proper COVID-19 protocols in place and families will need to complete the confirmation forms by April 30th to secure their child/ren’s spot in our program
If you were waitlisted, please click here for details regarding next steps.

Deadline #1: April 30

Confirmation Form

Confirm your family’s participation by completing the online Confirmation Form. Confirmation Form links are personalized to each family. A link was included in the email sent with your family’s registration information. If you need it re-sent, contact Ashton at

The Confirmation Form includes:

  • General Student Info and Medical Info
  • Swim Form and Scholarship Uploads
  • Courageous Medical, General Liability, and COVID-19 Waiver & Boston After School and Beyond City-Wide Measurement Project Waiver.

More information about 2021 course fees & payment

You may also find more detailed information about our Summer Youth Program in general, including what next steps are after the program,  in this student handbook.

If your child cannot attend the session s/he is registered for, please notify Ashton immediately at so that another child can be given the opportunity to sail.
Due to extremely high demand for this program, attendance is required at all classes.
Scholarship materials

If you received a scholarship, confirm your scholarship by providing Courageous Sailing with one or more of the following by April 30: Documents should be securely uploaded here.

  • 2020 Federal Income Tax Form 1040 (first page only, social security numbers blacked out)
  • Proof of being a government assistance beneficiary (ex. public housing, etc.)
  • Optional: Attach a separate page detailing any other information that may be helpful in determining financial need and extenuating circumstances.

Scholarship materials will be reviewed solely by the Programs and Operations Director, the Executive Director and/or their administrative assistants. After review, these sensitive documents will be destroyed immediately. For security purposes please black out Social Security numbers on all documents you upload to Courageous.

More information about scholarships

Deadline #2: Before Start of Program

Swimming Form

Print, have a lifeguard sign off on and submit the Proof of Swimming Form prior to your child(ren)’s first day of program. Upload the completed swim form with the Confirmation Form. As proof of your child’s or children’s swimming ability, the following documents qualify:

  • YMCA: Certificate of completion for Fish Level and/or Level 5 or above
  • Red Cross: Certificate of Completion for Level V or above
  • Boy/Girl Scouts: Swimming or Lifesaving Merit Badge
  • Courageous Sailing Swim Form
Download the Proof of Swimming Form
Blank proof of swimming forms may be downloaded here: Blank Swim Form

Complete one form per student. If you have already submitted this form for a previous program or season at Courageous Sailing, we have it on file and there is no need to submit another.

If you know that your child is not able to swim at least 25 yards (one pool lap) and stay afloat for at least 90 seconds without floatation or other assistance, please email us immediately.

Scholarship Information

Courageous Sailing is committed to providing high quality summer sailing programs to children of Greater Boston regardless of ability to pay. Scholarships are readily available for all who qualify. Extenuating circumstances are always taken into consideration should a family choose to share them with our staff.

  • Full scholarships ($0 class fees) are available to families on government assistance or with a household income of < $70,000.
  • Partial scholarships (~50% discount) are available to those with a household income between $70,000 and $140,000.
  • All siblings are 10% off.

Please Note: If your income puts you in a fee bracket that you can’t afford, we will work with you so that your children will be able to attend.

2021 Course Fees and Payment

The amount of fees owed were sent to you with your registration confirmation. This amount reflects anticipated scholarships. You can pay this invoice online with a credit card via a personalized link included in your registration packet. To receive the link again, contact You can also pay by submitting a check (payable to “Courageous Sailing”) or by dropping off cash at Courageous Sailing.

Barring the cancellation of programs, a full refund will only be given to families that withdraw before April 30th. After that date or without notification of withdrawal, no refund will be issued except for in extenuating circumstances.

A note on class fee increases in 2021: Courageous Sailing is committed to providing high-quality sailing programs to youth in the Boston area regardless of their ability to pay.

In the last few years, we’ve made major investments to grow our capacity – enabling a significant increase in available program spots. We’ve done this while improving program quality, keeping the majority of our classes three weeks in duration, and maintaining one of the lowest students to instructor ratios among Boston-area youth programs.

In order to help us continue to provide opportunities for all current students, and increase capacity to accept new students, we have gradually been increasing class fees to better offset our real costs per student (currently $600 per week). We remain committed to providing sailing programs to youth regardless of ability to pay, which means:

  • Scholarships continue to be readily available for all who qualify.
  • We do not want this increase in class fees to be a barrier for any new or returning student. We are committed to working with every family to ensure that your children will be able to attend.
  • The registration and lottery process for admittance to the Courageous Sailing Summer youth programs is “Need-Blind.” This means that admission, in no respect, is based on ability to pay.

By helping us to cover the true costs of programming, we will be able to direct more of our fundraising efforts to the following capacity-building priorities:

  • Increasing class offerings program-wide
  • Purchasing the dinghies we’ll need in the coming years to accommodate the growing number of advanced sailors
  • Maintaining our current fleet and replacing aging boats
  • Purchasing a fleet of boats for our burgeoning Jamaica Pond program
  • Paying our instructors industry competitive rates

Please don’t hesitate to contact Ashton, Programs and Operations Director, at with any questions, concerns, or if the fee bracket you fall in is a barrier to participation.

Please check out the frequently asked questions page.
For any additional questions or concerns, please contact Ashton, Programs and Operations Director,